Beginner Houseplants: DRACENA HELP PLEASE!!

I have had this dracena plant and it is has been mediocre at best for the past few years. I can never tell if i am over or underwatering it. I have it indoors with indirect east facing light. I really want to enhance its growth and see it thrive. today, its leaves fell off once again (once i run my hand through it). the fallen leaves are a yellowish/brown (see pics). can someone please advise me on if it looks like it needs more or less water, more or less light, re potting? anything to help it grow better!! thank you!!!

It's hard to say for sure from the pictures...overwatering and underwatering can have similar symptoms. Overwatering is a far more common problem though--to check if that's what is happening, before you would water it next try sticking your finger down a few inches into the pot and see how wet it feels. If it still feels wet, then you've been watering it too much. Also make sure that you have it in a pot that has a drainage hole, and if it does but you keep the pot in a saucer to prevent water from making a mess, make sure you empty the saucer promptly so you don't leave it sitting in water.

The moist soil is likely the culprit for any health issues your plant is having. Or, more specifically, the damage such can do to roots when the condition is prolonged, without a chance for the roots to reach some air as well as moisture. A soil that is composed of mostly fine particles, like peat, can often be what is causing the difficulty. If the roots are healthy, or can be rehabilitated, and the light is sufficient, there's no reason not to expect your plant to recover its' health, assuming it doesn't have some kind of virus or fungus.

Indirect east light doesn't sound like enough. Your tree would do much better with some direct light

When soil dries quickly (because it does not retain excess water, not just because it's too packed full of roots,) that is what is healthy for almost any house plants. Sitting in soggy soil is an unnatural state that usually/often causes roots to rot. When that happens, the roots are unable to deliver moisture and nutrients to the foliage. For a healthier plant, the soil should be chunky, porous, airy, not containing fine particles that behave like a sponge, holding water forever until they're suddenly completely dry and water just runs off.

It's usually recommended to wait until the days are longer, the rays are stronger to repot house plants, but I might do it pretty quick for this particular plant because I suspect it may be unable to regain its' health in the current conditions. If you'd like to wait to repot, when it does finally dry out, take it to a sink or shower and gently flood it with water, flushing the entire surface and contents thoroughly, then make sure it is finished dripping before putting the pot back on the drip saucer.

Leaving water sitting in the drip tray is something to which roots will have adverse reactions. Add some water chemicals, which can stay in the pot for extended periods if it's not drying quickly and being flushed once in a while, and you end up with a sick plant.

I didn't complete the thought process above, but if the soil dries quickly, you may find you are watering more often than before, when it was too much. As temps go up, sun gets more intense, even more. When changing soil types/textures, keep a close eye on plants so you get the new hang of how it's going to go. Just want to make sure I didn't leave the impression it should be dry all of the time. You want to water as often as needed for some moisture to stay in the pot, and not worry about excess water messing things up. Very few plants actually want to go bone dry at any time.

It's not about how much water you put on, it's about how much excess stays in the pot. That's what you're trying to avoid, as much as possible with your schedule and time available for plant caring. If it needs to be able to go for a week without water, a bigger pot is usually what I choose, not a more water-retentive mix. Good luck with your tree!